| Affiliation: | 1. Departamento de Química Orgánica (Universidad de Sevilla) and Centro, de Innovación en Química Avanzada (ORFEO-CINQA), C/ Prof. García González 1, 41012 Sevilla, Spain;2. Departamento de Química Orgánica (Universidad de Sevilla) and Centro, de Innovación en Química Avanzada (ORFEO-CINQA), C/ Prof. García González 1, 41012 Sevilla, Spain These authors contributed equally to this work.;3. Instituto Investigaciones Químicas (CSIC-US) and Centro de Innovación en Química Avanzada (ORFEO-CINQA), C/ Américo Vespucio 49, 41092 Sevilla, Spain |
| Abstract: | The formal insertion of alkenes into aromatic chloro- and bromoalkynes takes place under cationic gold catalysis. This haloalkynylation reaction can be performed with cyclic, gem-disubstituted and monosubstituted alkenes, using BINAP, triazolo[4,3-b]isoquinolin-3-ylidene ligands or SPhos, respectively. The products were isolated in moderate to excellent yields and with complete diastereo- and regioselectivity; the halogen atom bonding the more substituted carbon of the alkene. Preliminary experiments showed that the enantioselective haloalkynylation of cyclopentene can be performed with (S)-BINAP to afford the insertion products with moderate to good enantioselectivities. |
